Bis(O,O′-di-p-tolyl­di­thio­phosphato-κ²S,S′)­nickel(II)

The title compound, [Ni(C₁₄H₁₄O₂PS₂)₂], consists of discrete molecules with the Ni atom chelated by both S atoms of the p-tolyl­di­thio­phosphate ligands in a bidentate manner in a four-coordinate environment. The mol­ecule has inversion symmetry about the Ni atom, and the geometry is nearly perfect square planar, with S—Ni—S chelate bond angles of 89.12 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.030
• wR factor = 0.083
• Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S1      ..       6.29 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S2      ..       6.58 su
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            S1  -NI1 -S1  -P1    -15.00100.00   2.765   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          5
            S2  -NI1 -S2  -P1    165.00100.00   2.765   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         19
            P1  -NI1 -P1  -O1     76.00100.00   2.765   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            P1  -NI1 -P1  -O2   -101.00100.00   2.765   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            P1  -NI1 -P1  -S2    -14.00100.00   2.765   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            P1  -NI1 -P1  -S1    172.00100.00   2.765   1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Bis(O,O'-di-p-tolyldithiophosphato-κ²S,S')nickel(II)

Crystal data

[Ni(C14H14O2PS2)2]	Z = 1
Mr = 677.39	F(000) = 350
Triclinic, P1	Dx = 1.446 Mg m^−3
a = 7.1884 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3158 (14) Å	Cell parameters from 4396 reflections
c = 12.1699 (18) Å	θ = 1.7–26.0°
α = 78.605 (2)°	µ = 1.03 mm^−1
β = 81.335 (2)°	T = 293 K
γ = 78.557 (2)°	Block, purple
V = 777.7 (2) Å^3	0.48 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEX diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	2789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 83.7 pixels mm^-1	θmax = 26.0°, θmin = 1.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→11
Tmin = 0.638, Tmax = 0.798	l = −14→14
8064 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0471P)^2 + 0.1517P] where P = (Fo^2 + 2Fc^2)/3
3031 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	1.0000	0.5000	0.0000	0.04015 (11)
S1	0.83981 (7)	0.32810 (6)	0.10454 (4)	0.05265 (15)
S2	1.15284 (7)	0.49485 (6)	0.14752 (4)	0.05311 (15)
P1	0.98029 (7)	0.35593 (5)	0.22444 (4)	0.04372 (13)
O1	0.84886 (19)	0.42237 (15)	0.32546 (11)	0.0522 (3)
O2	1.08360 (19)	0.20555 (15)	0.29290 (11)	0.0532 (3)
C1	0.5089 (3)	0.4516 (2)	0.36319 (17)	0.0539 (5)
H1	0.4991	0.5393	0.3107	0.065*
C2	0.3474 (3)	0.4047 (3)	0.42487 (18)	0.0585 (5)
H2	0.2281	0.4621	0.4135	0.070*
C3	0.3590 (3)	0.2750 (3)	0.50272 (18)	0.0601 (5)
C4	0.5379 (3)	0.1908 (3)	0.51718 (19)	0.0626 (5)
H4	0.5485	0.1021	0.5686	0.075*
C5	0.7009 (3)	0.2357 (2)	0.45680 (18)	0.0570 (5)
H5	0.8204	0.1782	0.4674	0.068*
C6	0.6844 (3)	0.3657 (2)	0.38120 (15)	0.0461 (4)
C7	0.1825 (4)	0.2272 (4)	0.5721 (2)	0.0869 (8)
H7A	0.1765	0.2455	0.6476	0.130*
H7B	0.1875	0.1230	0.5740	0.130*
H7C	0.0711	0.2827	0.5390	0.130*
C8	1.1682 (3)	−0.0173 (2)	0.2140 (2)	0.0675 (6)
H8	1.0408	−0.0291	0.2275	0.081*
C9	1.3066 (4)	−0.1217 (3)	0.1671 (2)	0.0792 (7)
H9	1.2709	−0.2044	0.1497	0.095*
C10	1.4946 (4)	−0.1055 (3)	0.14589 (19)	0.0684 (6)
C11	1.5431 (3)	0.0168 (3)	0.1741 (2)	0.0656 (6)
H11	1.6703	0.0291	0.1610	0.079*
C12	1.4087 (3)	0.1219 (2)	0.22133 (18)	0.0559 (5)
H12	1.4441	0.2039	0.2401	0.067*
C13	1.2225 (3)	0.1026 (2)	0.23983 (15)	0.0473 (4)
C14	1.6438 (5)	−0.2202 (3)	0.0944 (3)	0.1055 (11)
H14A	1.7214	−0.2775	0.1509	0.158*
H14B	1.7230	−0.1709	0.0338	0.158*
H14C	1.5817	−0.2849	0.0657	0.158*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.04168 (19)	0.03780 (18)	0.04014 (19)	−0.01007 (13)	−0.00313 (13)	−0.00280 (13)
S1	0.0608 (3)	0.0539 (3)	0.0472 (3)	−0.0265 (2)	−0.0067 (2)	−0.0009 (2)
S2	0.0568 (3)	0.0574 (3)	0.0483 (3)	−0.0241 (2)	−0.0107 (2)	0.0012 (2)
P1	0.0470 (3)	0.0418 (3)	0.0402 (3)	−0.0092 (2)	−0.00134 (19)	−0.00343 (19)
O1	0.0543 (8)	0.0490 (7)	0.0526 (8)	−0.0098 (6)	0.0034 (6)	−0.0134 (6)
O2	0.0558 (8)	0.0500 (8)	0.0439 (7)	−0.0002 (6)	0.0025 (6)	0.0002 (6)
C1	0.0593 (12)	0.0558 (11)	0.0439 (10)	0.0007 (9)	−0.0091 (9)	−0.0106 (9)
C2	0.0470 (11)	0.0765 (15)	0.0526 (12)	0.0006 (10)	−0.0085 (9)	−0.0220 (11)
C3	0.0536 (12)	0.0827 (15)	0.0493 (11)	−0.0183 (11)	−0.0009 (9)	−0.0211 (11)
C4	0.0642 (13)	0.0628 (13)	0.0560 (12)	−0.0140 (11)	−0.0032 (10)	0.0010 (10)
C5	0.0483 (11)	0.0588 (12)	0.0577 (12)	−0.0015 (9)	−0.0053 (9)	−0.0036 (10)
C6	0.0464 (10)	0.0500 (10)	0.0417 (9)	−0.0072 (8)	0.0003 (7)	−0.0128 (8)
C7	0.0644 (15)	0.124 (2)	0.0768 (17)	−0.0361 (15)	0.0072 (13)	−0.0195 (16)
C8	0.0625 (13)	0.0506 (12)	0.0885 (17)	−0.0173 (10)	−0.0052 (12)	−0.0051 (11)
C9	0.101 (2)	0.0435 (12)	0.0956 (19)	−0.0126 (12)	−0.0139 (16)	−0.0155 (12)
C10	0.0821 (16)	0.0512 (12)	0.0552 (12)	0.0107 (11)	0.0024 (11)	0.0001 (10)
C11	0.0544 (12)	0.0612 (13)	0.0687 (14)	−0.0010 (10)	0.0039 (10)	0.0011 (11)
C12	0.0552 (12)	0.0500 (11)	0.0609 (12)	−0.0088 (9)	−0.0061 (9)	−0.0068 (9)
C13	0.0522 (10)	0.0404 (9)	0.0426 (10)	−0.0033 (8)	0.0002 (8)	−0.0001 (7)
C14	0.134 (3)	0.0707 (17)	0.083 (2)	0.0332 (18)	0.0112 (18)	−0.0134 (15)

Geometric parameters (Å, º)

Ni1—S2^i	2.2298 (5)	C4—H4	0.9300
Ni1—S2	2.2298 (5)	C5—C6	1.365 (3)
Ni1—S1	2.2348 (5)	C5—H5	0.9300
Ni1—S1^i	2.2348 (5)	C7—H7A	0.9600
Ni1—P1	2.7914 (6)	C7—H7B	0.9600
Ni1—P1^i	2.7914 (6)	C7—H7C	0.9600
S1—P1	1.9782 (7)	C8—C13	1.359 (3)
S2—P1	1.9743 (7)	C8—C9	1.388 (3)
P1—O1	1.5830 (13)	C8—H8	0.9300
P1—O2	1.5877 (14)	C9—C10	1.370 (4)
O1—C6	1.414 (2)	C9—H9	0.9300
O2—C13	1.416 (2)	C10—C11	1.374 (3)
C1—C6	1.376 (3)	C10—C14	1.514 (3)
C1—C2	1.382 (3)	C11—C12	1.379 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.377 (3)	C12—C13	1.365 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.384 (3)	C14—H14A	0.9600
C3—C7	1.508 (3)	C14—H14B	0.9600
C4—C5	1.379 (3)	C14—H14C	0.9600
S2^i—Ni1—S2	180.00 (3)	C5—C4—H4	119.4
S2^i—Ni1—S1	90.88 (2)	C3—C4—H4	119.4
S2—Ni1—S1	89.12 (2)	C6—C5—C4	119.06 (19)
S2^i—Ni1—S1^i	89.12 (2)	C6—C5—H5	120.5
S2—Ni1—S1^i	90.88 (2)	C4—C5—H5	120.5
S1—Ni1—S1^i	180.000 (19)	C5—C6—C1	121.42 (18)
S2^i—Ni1—P1	135.416 (17)	C5—C6—O1	120.67 (17)
S2—Ni1—P1	44.584 (17)	C1—C6—O1	117.73 (17)
S1—Ni1—P1	44.670 (16)	C3—C7—H7A	109.5
S1^i—Ni1—P1	135.330 (16)	C3—C7—H7B	109.5
S2^i—Ni1—P1^i	44.584 (17)	H7A—C7—H7B	109.5
S2—Ni1—P1^i	135.416 (17)	C3—C7—H7C	109.5
S1—Ni1—P1^i	135.330 (16)	H7A—C7—H7C	109.5
S1^i—Ni1—P1^i	44.670 (16)	H7B—C7—H7C	109.5
P1—Ni1—P1^i	180.0	C13—C8—C9	118.7 (2)
P1—S1—Ni1	82.75 (2)	C13—C8—H8	120.7
P1—S2—Ni1	82.97 (2)	C9—C8—H8	120.7
O1—P1—O2	99.39 (7)	C10—C9—C8	121.5 (2)
O1—P1—S2	109.61 (6)	C10—C9—H9	119.3
O2—P1—S2	114.56 (6)	C8—C9—H9	119.3
O1—P1—S1	114.46 (6)	C9—C10—C11	117.8 (2)
O2—P1—S1	114.23 (6)	C9—C10—C14	120.8 (3)
S2—P1—S1	104.85 (3)	C11—C10—C14	121.3 (3)
O1—P1—Ni1	124.27 (6)	C10—C11—C12	121.9 (2)
O2—P1—Ni1	136.28 (5)	C10—C11—H11	119.0
S2—P1—Ni1	52.448 (18)	C12—C11—H11	119.0
S1—P1—Ni1	52.578 (19)	C13—C12—C11	118.4 (2)
C6—O1—P1	122.93 (12)	C13—C12—H12	120.8
C13—O2—P1	122.33 (11)	C11—C12—H12	120.8
C6—C1—C2	118.5 (2)	C8—C13—C12	121.70 (19)
C6—C1—H1	120.7	C8—C13—O2	118.89 (18)
C2—C1—H1	120.7	C12—C13—O2	119.32 (18)
C3—C2—C1	121.6 (2)	C10—C14—H14A	109.5
C3—C2—H2	119.2	C10—C14—H14B	109.5
C1—C2—H2	119.2	H14A—C14—H14B	109.5
C2—C3—C4	118.1 (2)	C10—C14—H14C	109.5
C2—C3—C7	121.1 (2)	H14A—C14—H14C	109.5
C4—C3—C7	120.7 (2)	H14B—C14—H14C	109.5
C5—C4—C3	121.3 (2)
S2^i—Ni1—S1—P1	−176.06 (2)	O2—P1—O1—C6	−73.46 (15)
S2—Ni1—S1—P1	3.94 (2)	S2—P1—O1—C6	166.14 (13)
S1^i—Ni1—S1—P1	−15 (100)	S1—P1—O1—C6	48.69 (15)
P1^i—Ni1—S1—P1	180.0	Ni1—P1—O1—C6	108.83 (13)
S2^i—Ni1—S2—P1	165 (100)	O1—P1—O2—C13	−179.14 (14)
S1—Ni1—S2—P1	−3.95 (2)	S2—P1—O2—C13	−62.43 (15)
S1^i—Ni1—S2—P1	176.05 (2)	S1—P1—O2—C13	58.54 (15)
P1^i—Ni1—S2—P1	180.0	Ni1—P1—O2—C13	−1.88 (19)
Ni1—S2—P1—O1	−118.70 (6)	C6—C1—C2—C3	−0.2 (3)
Ni1—S2—P1—O2	130.62 (6)	C1—C2—C3—C4	−0.7 (3)
Ni1—S2—P1—S1	4.62 (3)	C1—C2—C3—C7	178.1 (2)
Ni1—S1—P1—O1	115.53 (6)	C2—C3—C4—C5	0.9 (3)
Ni1—S1—P1—O2	−130.82 (6)	C7—C3—C4—C5	−177.9 (2)
Ni1—S1—P1—S2	−4.61 (3)	C3—C4—C5—C6	−0.2 (3)
S2^i—Ni1—P1—O1	−90.66 (7)	C4—C5—C6—C1	−0.8 (3)
S2—Ni1—P1—O1	89.34 (7)	C4—C5—C6—O1	174.12 (18)
S1—Ni1—P1—O1	−96.29 (7)	C2—C1—C6—C5	1.0 (3)
S1^i—Ni1—P1—O1	83.71 (7)	C2—C1—C6—O1	−174.06 (16)
P1^i—Ni1—P1—O1	76 (100)	P1—O1—C6—C5	75.9 (2)
S2^i—Ni1—P1—O2	92.61 (9)	P1—O1—C6—C1	−109.00 (18)
S2—Ni1—P1—O2	−87.39 (9)	C13—C8—C9—C10	−0.5 (4)
S1—Ni1—P1—O2	86.98 (9)	C8—C9—C10—C11	0.9 (4)
S1^i—Ni1—P1—O2	−93.02 (9)	C8—C9—C10—C14	−179.8 (2)
P1^i—Ni1—P1—O2	−101 (100)	C9—C10—C11—C12	−0.6 (4)
S2^i—Ni1—P1—S2	180.0	C14—C10—C11—C12	−179.8 (2)
S1—Ni1—P1—S2	174.38 (3)	C10—C11—C12—C13	−0.2 (3)
S1^i—Ni1—P1—S2	−5.62 (3)	C9—C8—C13—C12	−0.4 (3)
P1^i—Ni1—P1—S2	−14 (100)	C9—C8—C13—O2	−176.9 (2)
S2^i—Ni1—P1—S1	5.62 (3)	C11—C12—C13—C8	0.7 (3)
S2—Ni1—P1—S1	−174.38 (3)	C11—C12—C13—O2	177.16 (18)
S1^i—Ni1—P1—S1	180.0	P1—O2—C13—C8	−97.9 (2)
P1^i—Ni1—P1—S1	172 (100)	P1—O2—C13—C12	85.6 (2)

Symmetry code: (i) −x+2, −y+1, −z.